3-(1-phenyl-2-propynyl)-1-tert-butyldimethylsilylindole | 1004517-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(1-phenyl-2-propynyl)-1-tert-butyldimethylsilylindole
• 英文别名: tert-butyl-dimethyl-[3-[(1R)-1-phenylprop-2-ynyl]indol-1-yl]silane
• CAS: 1004517-26-3
• 化学式: C₂₃H₂₇NSi
• 分子量: 345.56
• InChiKey: VBHLTHPRAHVORJ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  N-tert-butyldimethylsilylindole 、 (+/-)-1-苯基-2-丙炔-1-醇 在 chiral di(1-phenyl)propyl disulfide-based ruthenium complex ammonium tetrafluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 3-(1-phenyl-2-propynyl)-1-tert-butyldimethylsilylindole 、 3-(1-phenyl-2-propynyl)-1-tert-butyldimethylsilylindole
  参考文献：
  名称：

  Remarkable Effect of N-Substituent on Enantioselective Ruthenium-Catalyzed Propargylation of Indoles with Propargylic Alcohols

  摘要：

  Ruthenium-catalyzed enantioselective propargylation of indoles with propargylic alcohols affords the corresponding beta-propargylated indoles in good yields with a high enantioselectivity (up to 95% ee). A remarkable effect of the nature of the N-substituent of indoles is observed for the enantioselectivity of the propargylated indoles. The preparative method described in this paper may provide a novel protocol for asymmetric Friedel-Crafts alkylation of indoles using propargylic alcohols as a new type of electrophiles.

  DOI：

  10.1021/ol7025203

文献信息

• Remarkable Effect of <i>N</i>-Substituent on Enantioselective Ruthenium-Catalyzed Propargylation of Indoles with Propargylic Alcohols
  作者：Hiroshi Matsuzawa、Keiichiro Kanao、Yoshihiro Miyake、Yoshiaki Nishibayashi

  DOI：10.1021/ol7025203

  日期：2007.12.1

  Ruthenium-catalyzed enantioselective propargylation of indoles with propargylic alcohols affords the corresponding beta-propargylated indoles in good yields with a high enantioselectivity (up to 95% ee). A remarkable effect of the nature of the N-substituent of indoles is observed for the enantioselectivity of the propargylated indoles. The preparative method described in this paper may provide a novel protocol for asymmetric Friedel-Crafts alkylation of indoles using propargylic alcohols as a new type of electrophiles.